CA2006430A1 - Procede pour neutraliser des fluides organiques - Google Patents
Procede pour neutraliser des fluides organiquesInfo
- Publication number
- CA2006430A1 CA2006430A1 CA002006430A CA2006430A CA2006430A1 CA 2006430 A1 CA2006430 A1 CA 2006430A1 CA 002006430 A CA002006430 A CA 002006430A CA 2006430 A CA2006430 A CA 2006430A CA 2006430 A1 CA2006430 A1 CA 2006430A1
- Authority
- CA
- Canada
- Prior art keywords
- finely divided
- divided solid
- liquid mixture
- neutralization
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 47
- 230000008569 process Effects 0.000 title claims abstract description 44
- 238000006386 neutralization reaction Methods 0.000 title claims abstract description 42
- 239000012530 fluid Substances 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 42
- 239000007787 solid Substances 0.000 claims abstract description 27
- 239000007788 liquid Substances 0.000 claims abstract description 21
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 8
- 230000007935 neutral effect Effects 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 239000007791 liquid phase Substances 0.000 claims abstract description 5
- 239000007790 solid phase Substances 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims description 53
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 26
- 235000011116 calcium hydroxide Nutrition 0.000 claims description 26
- 239000000920 calcium hydroxide Substances 0.000 claims description 25
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 25
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 229910001868 water Inorganic materials 0.000 claims description 18
- 239000000292 calcium oxide Substances 0.000 claims description 11
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 9
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 claims description 7
- 229910001701 hydrotalcite Inorganic materials 0.000 claims description 7
- 229960001545 hydrotalcite Drugs 0.000 claims description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 239000000395 magnesium oxide Substances 0.000 claims description 5
- -1 alkaline earth metal carbonates Chemical class 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims 3
- 230000005494 condensation Effects 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000003377 acid catalyst Substances 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims 1
- 239000000347 magnesium hydroxide Substances 0.000 claims 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 239000011575 calcium Substances 0.000 abstract description 14
- 150000004679 hydroxides Chemical class 0.000 abstract description 9
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 230000002378 acidificating effect Effects 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- 150000003839 salts Chemical class 0.000 abstract description 7
- 150000001342 alkaline earth metals Chemical class 0.000 abstract description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052791 calcium Inorganic materials 0.000 abstract description 4
- 239000000470 constituent Substances 0.000 abstract description 4
- 229910052749 magnesium Inorganic materials 0.000 abstract description 4
- 239000011777 magnesium Substances 0.000 abstract description 4
- 229910001038 basic metal oxide Inorganic materials 0.000 abstract description 3
- 238000000926 separation method Methods 0.000 abstract description 3
- 239000007858 starting material Substances 0.000 abstract description 3
- 239000003513 alkali Substances 0.000 abstract description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract description 2
- 239000012074 organic phase Substances 0.000 abstract description 2
- 239000000159 acid neutralizing agent Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 31
- 239000003795 chemical substances by application Substances 0.000 description 22
- 230000003472 neutralizing effect Effects 0.000 description 21
- 239000007795 chemical reaction product Substances 0.000 description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 17
- 239000003112 inhibitor Substances 0.000 description 12
- 239000012043 crude product Substances 0.000 description 10
- 235000012255 calcium oxide Nutrition 0.000 description 8
- 238000005886 esterification reaction Methods 0.000 description 8
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 7
- 230000032050 esterification Effects 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 230000002411 adverse Effects 0.000 description 3
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 3
- 229940043430 calcium compound Drugs 0.000 description 3
- 150000001674 calcium compounds Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001879 gelation Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 125000004386 diacrylate group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 229910020038 Mg6Al2 Inorganic materials 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- GANNOFFDYMSBSZ-UHFFFAOYSA-N [AlH3].[Mg] Chemical compound [AlH3].[Mg] GANNOFFDYMSBSZ-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000001668 ameliorated effect Effects 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000010952 in-situ formation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 238000013386 optimize process Methods 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000004224 protection Effects 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/62—Use of additives, e.g. for stabilisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3843843.7 | 1988-12-24 | ||
| DE3843843A DE3843843A1 (de) | 1988-12-24 | 1988-12-24 | Verfahren zur verbesserten herstellung von (meth)acrylsaeureestern mehrwertiger alkohole (iv) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2006430A1 true CA2006430A1 (fr) | 1990-06-24 |
Family
ID=6370228
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002006432A Abandoned CA2006432A1 (fr) | 1988-12-24 | 1989-12-21 | Procede pour ameliorer la production d'esters d'acide (meth)acrylique et de polyols (iv) |
| CA002006430A Abandoned CA2006430A1 (fr) | 1988-12-24 | 1989-12-21 | Procede pour neutraliser des fluides organiques |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002006432A Abandoned CA2006432A1 (fr) | 1988-12-24 | 1989-12-21 | Procede pour ameliorer la production d'esters d'acide (meth)acrylique et de polyols (iv) |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5159106A (fr) |
| EP (2) | EP0449919B1 (fr) |
| JP (1) | JP2758717B2 (fr) |
| AU (1) | AU618875B2 (fr) |
| CA (2) | CA2006432A1 (fr) |
| DE (2) | DE3843843A1 (fr) |
| ES (1) | ES2053171T3 (fr) |
| WO (1) | WO1990007483A1 (fr) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3843854A1 (de) * | 1988-12-24 | 1990-06-28 | Henkel Kgaa | Verfahren zur verbesserten herstellung von (meth)acrylsaeureestern mehrwertiger alkohole (i) |
| DE3843930A1 (de) * | 1988-12-24 | 1990-06-28 | Henkel Kgaa | Verfahren zur verbesserten herstellung von (meth)acrylsaeureestern mehrwertiger alkohole (iii) |
| DE4037516A1 (de) * | 1990-11-26 | 1992-05-27 | Henkel Kgaa | Hochfeste und abbaubare werkstoffe und formkoerper fuer die implantation in den menschlichen und tierischen organismus |
| DE4140373A1 (de) * | 1991-12-07 | 1993-06-09 | Henkel Kgaa, 4000 Duesseldorf, De | Verbesserte trockenneutralisation olefinisch reaktiver organischer fluessigphasen |
| US6353061B1 (en) | 1993-05-26 | 2002-03-05 | Dentsply Gmbh | α, ω-methacrylate terminated macromonomer compounds |
| US6369164B1 (en) | 1993-05-26 | 2002-04-09 | Dentsply G.M.B.H. | Polymerizable compounds and compositions |
| US5998499A (en) | 1994-03-25 | 1999-12-07 | Dentsply G.M.B.H. | Liquid crystalline (meth)acrylate compounds, composition and method |
| CA2146816A1 (fr) | 1994-04-22 | 1995-10-23 | Joachim E. Klee | Methode et composition pour la preparation d'un produit polymerique dentaire |
| DE19638093A1 (de) † | 1996-09-18 | 1998-03-19 | Basf Ag | Verfahren zur Vermeidung, Entfernung oder Verminderung von Ablagerungen an Apparateteilen bei der Veresterung von Acryl- oder Methacrylsäure |
| US5859280A (en) * | 1997-07-01 | 1999-01-12 | Betzdearborn Inc. | Methods for inhibiting the polymerization of vinyl monomers |
| JP3787261B2 (ja) | 1999-04-16 | 2006-06-21 | 株式会社日本触媒 | 易重合性化合物の重合防止方法 |
| JP4698778B2 (ja) | 1999-06-03 | 2011-06-08 | 株式会社日本触媒 | （メタ）アクリル酸（エステル）の精製方法 |
| DE19937911A1 (de) | 1999-08-11 | 2001-02-15 | Cognis Deutschland Gmbh | Verfahren zum Herstellen von Estern aus ungesättigten Carbonsäuren und mehrwertigen Alkoholen |
| DE10131479B4 (de) * | 2001-06-29 | 2005-05-19 | Röhm GmbH & Co. KG | Farbstabilisierung von grundstabilisierten ethylenisch ungesättigten Monomeren, insbesondere von grundstabilisierten Hydroxyalkyl(meth)acrylaten |
| WO2003064370A1 (fr) * | 2002-01-30 | 2003-08-07 | Mitsubishi Chemical Corporation | Procede de production d'ester (meth)acrylique |
| US20030191338A1 (en) * | 2002-04-09 | 2003-10-09 | Johnston Allen D. | Methods for inhibiting the polymerization of methacrylate monomers |
| DE10225943A1 (de) | 2002-06-11 | 2004-01-08 | Basf Ag | Verfahren zur Herstellung von Estern von Polyalkoholen |
| JP2006169220A (ja) * | 2004-12-20 | 2006-06-29 | Osaka Organic Chem Ind Ltd | （メタ）アクリル酸エステルの製造法 |
| US8772532B2 (en) * | 2011-08-03 | 2014-07-08 | Cognis Ip Management Gmbh | Process for preparing (meth)acrylic esters of polyols |
| ES2720326T3 (es) | 2011-08-03 | 2019-07-19 | Cognis Ip Man Gmbh | Procedimiento para preparar ésteres de ácido (met)acrílico de polioles |
| JP2013189415A (ja) * | 2012-03-15 | 2013-09-26 | Mitsubishi Rayon Co Ltd | ポリテトラメチレンエーテルグリコールジ（メタ）アクリレートの製造方法 |
| FR3008899B1 (fr) * | 2013-07-25 | 2017-04-21 | Arkema France | Methode et systeme pour la distribution d'un liquide dans des capacites pour la preparation de monomeres (meth)acryliques |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL22878A (en) * | 1965-01-31 | 1968-09-26 | Schachter H | Production of insulating sleeves for pipes |
| DE1779712A1 (de) * | 1968-09-14 | 1971-09-09 | Wilhelm Lehnhardt | Vorrichtung zum Herstellen von in sich geschlossenen Bauteilen,insbesondere Fensterrahmen u.dgl.aus von einem glasfaserverstaerkten Giessharzmantel umgebenen Kern |
| FR2180893B1 (fr) * | 1972-04-18 | 1976-05-28 | Union Carbide Corp | |
| US3988213A (en) * | 1972-09-25 | 1976-10-26 | Nippon Shokubai Kagaku Kogyo Co., Ltd. | Method of distilling vinyl compounds |
| US4512910A (en) * | 1982-01-28 | 1985-04-23 | Morton Thickol, Inc. | Photocurable compositions |
| US4511732A (en) * | 1982-03-15 | 1985-04-16 | Celanese Corporation | Low viscosity UV curable polyacrylates |
| US4859792A (en) * | 1986-08-01 | 1989-08-22 | Hoechst Celanese Corp. | Accelerated preparation of esters |
| JPH01165349A (ja) * | 1987-12-21 | 1989-06-29 | Katsuhiko Komiyama | おにぎり及びおにぎりの製造方法 |
| DE3843854A1 (de) * | 1988-12-24 | 1990-06-28 | Henkel Kgaa | Verfahren zur verbesserten herstellung von (meth)acrylsaeureestern mehrwertiger alkohole (i) |
| DE3843938A1 (de) * | 1988-12-24 | 1990-06-28 | Henkel Kgaa | Verfahren zur verbesserten herstellung von (meth)acrylsaeureestern mehrwertiger alkohole (ii) |
| DE3843930A1 (de) * | 1988-12-24 | 1990-06-28 | Henkel Kgaa | Verfahren zur verbesserten herstellung von (meth)acrylsaeureestern mehrwertiger alkohole (iii) |
-
1988
- 1988-12-24 DE DE3843843A patent/DE3843843A1/de not_active Withdrawn
-
1989
- 1989-12-15 DE DE58907626T patent/DE58907626D1/de not_active Expired - Lifetime
- 1989-12-15 US US07/679,073 patent/US5159106A/en not_active Expired - Lifetime
- 1989-12-15 ES ES90900865T patent/ES2053171T3/es not_active Expired - Lifetime
- 1989-12-15 EP EP90900865A patent/EP0449919B1/fr not_active Expired - Lifetime
- 1989-12-15 WO PCT/EP1989/001546 patent/WO1990007483A1/fr active IP Right Grant
- 1989-12-15 JP JP2501465A patent/JP2758717B2/ja not_active Expired - Lifetime
- 1989-12-15 EP EP89123221A patent/EP0377156A1/fr not_active Withdrawn
- 1989-12-21 CA CA002006432A patent/CA2006432A1/fr not_active Abandoned
- 1989-12-21 CA CA002006430A patent/CA2006430A1/fr not_active Abandoned
-
1990
- 1990-02-12 AU AU49716/90A patent/AU618875B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| ES2053171T3 (es) | 1994-07-16 |
| DE58907626D1 (de) | 1994-06-09 |
| EP0449919B1 (fr) | 1994-05-04 |
| US5159106A (en) | 1992-10-27 |
| JP2758717B2 (ja) | 1998-05-28 |
| JPH04502459A (ja) | 1992-05-07 |
| EP0449919A1 (fr) | 1991-10-09 |
| WO1990007483A1 (fr) | 1990-07-12 |
| CA2006432A1 (fr) | 1990-06-24 |
| EP0377156A1 (fr) | 1990-07-11 |
| DE3843843A1 (de) | 1990-07-05 |
| AU4971690A (en) | 1991-08-29 |
| AU618875B2 (en) | 1992-01-09 |
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